Water → N-(4-chloromethylphenyl)-7-(4-ethoxyphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide

To a suspension of 7-(4-ethoxyphenyl)-N-(4-hydroxymethylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (2.55 g) and pyridine (2 drops) in chloroform (50 ml) was added thionyl chloride (0.8 ml) at room temperature, and the mixture was stirred for 20 hours. To the reaction mixture was added water and then THF, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure to give solid, which was dissolved in THF and ethyl acetate. The mixture was concentrated under reduced pressure to give crystals, which were collected by filtration and washed with diisopropylether to give N-(4-chloromethylphenyl)-7-(4-ethoxyphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (2.42 g) as colorless crystals.

1. extractionTHF, and the mixture was extracted with ethyl acetate
2. washThe organic layer was washed with saturated sodium chloride solution
3. dry with materialdried with magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. customto give solid, which
6. concentrationThe mixture was concentrated under reduced pressure
7. customto give crystals, which
8. filtrationwere collected by filtration
9. washwashed with diisopropylether

ORD record

ord-c4a9f4328dad493b91eddd6c79916287

Source dataset

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06096780